Aldol
Condensation
Summary:
The Aldol Condensation is an important carbon-carbon bond forming reaction. In this
classic reaction, an a, b-unsaturated carbonyl compound is formed by a crossed-aldol
condensation.
Reference: Preparation of trans-p-Anisalacetophenone, Experimental Organic chemistry, 2011, 5th Edition, Gilbert
and Martin, p. 620.
Chemical Name Amount per 100 Purchasing cost per 100
EH&S
Aldrich Catalog # students (g or mL) students ($)
p-anisaldehyde
A88107 10 mL $4.29
Acetophenone
A10701 10 mL $1.95
Sodium hydroxide *C
221465 25 g $2.88
Water
n/a 25 mL n/w
Ethanol, 95%
459836 50 mL $3.88
Methanol
322415 500 mL $25.17
Aldol Condensation: Greener Approach
Summary:
This solventless aldol condensation* allows for students to perform a based-
catalyzed reaction by grinding two raw materials together and witnessing the melting
of the reactants for the reaction to occur. The product is produced through aqueous
work-up and recrystallized in ethanol/water.
Reference: Solventless Reactions: The Aldol Reaction, Green Organic Chemistry – Strategies, Tools, and
Laboratory Experiments, Doxsee, K.M. And Hutchison, J.E., Tompson Brooks/Cole, 2004, pp. 115-119
Chemical Name Amount per Purchasing cost per
Aldrich Catalog # 100 100 students ($)
EH&S
students (g
or mL)
3,4-dimethoxybenzaldehyde
12.5 g $3.65
143758
1-indanone
10 g $37.00
I2304
*C
sodium hydroxide
2.5 g $0.29
221465
Hydrochloric acid, 3M
100 mL $0.98
320331
Ethanol, 90%
750 mL $3.64
792799
Aldol Condensation: Greener Approach
Summary:
This solventless aldol condensation is the solvent-free synthesis of chalcones, made by mixing and matching
various aldehydes and acetophenones. The reactions proceed by grinding in a mortar and pestle. The work-
up of the chalcones are simple, involving only water. The final product can be recrystallized in ethanol,
ethanol-water, or ethanol-toluene, depending on the product (see primary literature for typical yields and
tables with properties of the product.
Reference: Solvent-free Synthesis of Chalcones, J. Chem. Educ., 2004, 81, 1345
Chemical Name Amount per 100 Purchasing cost per
EH&S
Aldrich Catalog # students (g or mL) 100 students ($)
One of the following p-anisaldehyde 34 g
aldehydes are used A88107 $4.71
(the amounts listed
are the total
p-tolualdehyde 30 g $7.43
amounts for each
T35602
aldehyde needed if
only that aldehyde
was selected): 4-chlorobenzaldehyde 35 g $5.58
112216
3-chlorobenzaldehyde 35 g $44.57
C23403
Benzaldehyde 26.5 g $9.04
B1334
One of the Acetophenone 29 mL $5.09
following A10701
acetophenones are
used (the amounts 4’-methylacetophenone 37.5 g $6.44
listed are the total M26615
amounts for each
acetophenone 4’-bromoacetophenone 50 g $28.99
needed if only that B56404
acetophenone was
selected):
4’-methoxyacetophenone 33.5 g $7.99
117374
Sodium hydroxide 10 g *C
221465 $1.04
Water
n/a 1000 mL n/w
Ethanol, 95%
459836 500 mL $3.88
Toluene 250 mL $9.43
244511
Comparison: Aldol Condensation
Comparison of greener and traditional lab:
• Greener methods introduces the concepts of solvent-free synthesis. However, solvents are
required in the work-up of the reaction to produce the product.
• Greener processes avoids the use of methanol
• Purchasing costs are comparable
Purchasing costs Waste (per 100 “Greener” benefits
students)
Greener method – $48.25 875 mL liquid waste
solventless aldol
Greener method – $24.15 - $87.91* 1 L liquid aqueous
solventless synthesis waste
of chalcones ~500 mL solvent waste
(recrystallization)
Traditional method $45.56 620 mL liquid waste
Other greener lab options to explore:
• Green Chemistry Laboratory: Benign Synthesis of 4,6-Diphenyl[2,2']bipyridine via Sequential
Solventless Aldol and Michael Additions, J. Chem. Educ. 2005, 82, 468-469
• A Green Enantioselective Aldol Condensation for the Undergraduate Organic Laboratory, J. Chem.
Educ. 2006, 83, 1871-1872
• The Aldol Addition and Condensation: The Effect of Conditons on the Reaction Pathway, J. Chem.
Educ. 2007, 84, 475-476
* Purchasing cost depends on the aldehyde and acetophenone used in the experiment.
* Very high hazard
EHS Key: Physical hazard High hazard
Toxicity/Health hazard Moderate hazard
PBT Low hazard
No data
